Electrophilic 5-endo-trig cyclisations of 2-silyl-3-alkenols. A stereoselective route to polysubstituted tetrahydrofurans

Article abstract of DOI:10.1016/S0040-4020(97)00109-9

Electrophilic 5-endo-trig cyclisations of allylsilanes have been carried out leading to tri- and tetrasubstituted tetrahydrofurans with reasonable yields and excellent diastereoselectivities. A rationalization of both the regio- and the stereoselectivity has been proposed. A silicon group having a thienyl fragment attached to the silicon has also been devised and was shown to be oxidized under both electrophilic and nucleophilic conditions.